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Top Dodecanese Sailing Trips

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Sunset Cruise with Greek BBQ & Unlimited Aperol Spritz, Beer Wine

Start your relaxing 3 hour sunset cruise from Mandraki Harbour, where you will head to Kalithea Springs for a swim and to relax. You'll also …More

Rhodes, Greece
4.7 (153)

Sunset Cruise with Greek BBQ & Unlimited Aperol Spritz, Beer Wine

Start your relaxing 3 hour sunset cruise from Mandraki Harbour, where you will head to Kalithea Springs for a swim and to relax. You'll also...

3 hours • Free Cancellation
4.7 (153)
from
$47
Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks

If you are you looking for a relaxing and memorable day trip from Athens, look no further than a full-day cruise on a traditional wooden …More

Rhodes, Greece
4.8 (623)

Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks

If you are you looking for a relaxing and memorable day trip from Athens, look no further than a full-day cruise on a traditional wooden...

10 hours • Hotel pickup offered • Free Cancellation
4.8 (623)
from
$158
Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks

Our Sun & Sea Cruise is designed for those holiday makers looking for a chilled cruise and a true taste of first class Greek Hospitality. …More

Rhodes, Greece
4.8 (614)

Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks

Our Sun & Sea Cruise is designed for those holiday makers looking for a chilled cruise and a true taste of first class Greek Hospitality....

6 hours • Free Cancellation
4.8 (614)
from
$76
Private Full-Day Cruise in Rhodes with Lunch and Drinks

We organise daily cruises,along the eastern coast of Rhodes Island.Our trip is one of the most relaxing and adventurous tours on the island.We have three …More

Rhodes, Greece
5.0 (218)

Private Full-Day Cruise in Rhodes with Lunch and Drinks

We organise daily cruises,along the eastern coast of Rhodes Island.Our trip is one of the most relaxing and adventurous tours on the island.We have three...

6 hours 30 minutes • Free Cancellation
5.0 (218)
from
$855
All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea

Experience the ultimate day of sun, sea, and Greek hospitality. This is our most popular tour for a reason: it combines the three most iconic …More

Rhodes, Greece
4.8 (236)

All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea

Experience the ultimate day of sun, sea, and Greek hospitality. This is our most popular tour for a reason: it combines the three most iconic...

6 hours • Hotel pickup offered • Free Cancellation
4.8 (236)
from
$90
Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours

We sail from Marina Mandraki (port) at 10:00am. Enjoy travelling with our traditional wooden boat to one of the most impressive beaches of Rhodes, the …More

Rhodes, Greece
4.8 (473)

Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours

We sail from Marina Mandraki (port) at 10:00am. Enjoy travelling with our traditional wooden boat to one of the most impressive beaches of Rhodes, the...

5 hours 30 minutes • Free Cancellation
4.8 (473)
from
$66
Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim

Take in the beautiful Mediterranean ocean and views from a boat with swim and snorkeling stops along the way. Taste locally-made Greek dishes at lunchtime, …More

Kos, Greece
4.9 (99)

Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim

Take in the beautiful Mediterranean ocean and views from a boat with swim and snorkeling stops along the way. Taste locally-made Greek dishes at lunchtime,...

7 hours • Free Cancellation
4.9 (99)
from
$169
Catamaran Cruises Rhodes - 6 Hours Day Cruise ALL INCLUSIVE

**Live the Catamaran experience in Rhodes** We offer our clients the comfort and pleasure of luxury cruises around the beautiful island of Rhodes, creating an …More

Rhodes, Greece
4.7 (224)

Catamaran Cruises Rhodes - 6 Hours Day Cruise ALL INCLUSIVE

**Live the Catamaran experience in Rhodes** We offer our clients the comfort and pleasure of luxury cruises around the beautiful island of Rhodes, creating an...

6 hours • Free Cancellation
4.7 (224)
from
$99
Semi-Private Sailing Cruise to Iconic Bays (Shore-Ex Top Choice)

Escape the large tour boats and experience the Rhodes coastline in total serenity. Join us on a boutique sailing yacht for a semi-private journey limited …More

Rhodes, Greece
4.9 (172)

Semi-Private Sailing Cruise to Iconic Bays (Shore-Ex Top Choice)

Escape the large tour boats and experience the Rhodes coastline in total serenity. Join us on a boutique sailing yacht for a semi-private journey limited...

6 hours • Hotel pickup offered • Free Cancellation
4.9 (172)
from
$117
Full/Half Day Small Group Boat Trip with Food and Drinks

Experience sailing with the wind on this semi-private trip limited to 13 people but aiming for no more than 10 each time. After leaving Lindos …More

Rhodes, Greece
4.9 (87)

Full/Half Day Small Group Boat Trip with Food and Drinks

Experience sailing with the wind on this semi-private trip limited to 13 people but aiming for no more than 10 each time. After leaving Lindos...

5 hours 30 minutes • Free Cancellation
4.9 (87)
from
$70
Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim

Discover the Magic of the Aegean on a Catamaran Day Cruise from Kos! Set sail on a spacious catamaran as we journey from Kos to …More

Kos, Greece
4.9 (96)

Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim

Discover the Magic of the Aegean on a Catamaran Day Cruise from Kos! Set sail on a spacious catamaran as we journey from Kos to...

7 hours • Free Cancellation
4.9 (96)
from
$204
Lindos Full Day Boat Tour with Swimming

Our personnel is annually trained for the sole purpose of providing our customers maximum safety and comfortability that their money can buy. Our unique destinations …More

Rhodes, Greece
4.6 (137)

Lindos Full Day Boat Tour with Swimming

Our personnel is annually trained for the sole purpose of providing our customers maximum safety and comfortability that their money can buy. Our unique destinations...

8 hours • Free Cancellation
4.6 (137)
from
$47
3-Hours Sunset Catamaran Cruise with Dinner all Inclusive

The Sunset Cruise will exploit your senses. Start your relaxing sunset cruise from Mandraki Harbor. Set sail to Kalithea Springs for a swim and relaxing. …More

Likely to Sell Out
Likely to Sell Out
Rhodes, Greece
4.9 (46)

3-Hours Sunset Catamaran Cruise with Dinner all Inclusive

The Sunset Cruise will exploit your senses. Start your relaxing sunset cruise from Mandraki Harbor. Set sail to Kalithea Springs for a swim and relaxing....

3 hours • Free Cancellation
4.9 (46)
from
$82
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail

Sail in Style Aboard the Newly Renovated Sailing Edisa ⛵ Sailing Edisa offers a private luxury yacht experience designed for guests who value privacy, comfort, …More

Rhodes, Greece
5.0 (71)

Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail

Sail in Style Aboard the Newly Renovated Sailing Edisa ⛵ Sailing Edisa offers a private luxury yacht experience designed for guests who value privacy, comfort,...

6 hours • Free Cancellation
5.0 (71)
from
$1,071
Luxury Catamaran Morning Semi-Private and Greek Gastronomy Athens

More Than Just a Cruise, It's an Experience. Our Athenian Riviera cruise is more than just a day at sea. It's a unique and unforgettable …More

Halkidiki, Greece
5.0 (61)

Luxury Catamaran Morning Semi-Private and Greek Gastronomy Athens

More Than Just a Cruise, It's an Experience. Our Athenian Riviera cruise is more than just a day at sea. It's a unique and unforgettable...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (61)
from
$193
Private sunset cruise in Rhodes with fruits and drinks.

The sunset trip is one of the best evening tour that you can go to,if you want a relaxing time. You can see some historical …More

Rhodes, Greece
5.0 (58)

Private sunset cruise in Rhodes with fruits and drinks.

The sunset trip is one of the best evening tour that you can go to,if you want a relaxing time. You can see some historical...

3 to 4 hours • Free Cancellation
5.0 (58)
from
$450
Sunset Cruise in Rhodes with unlimited drinks & snacks

Kallithea springs is a popular swimming spot. The thermal springs of Kallithea in Rhodes were known from the ancient times for the beneficial properties of …More

Rhodes, Greece
4.9 (70)

Sunset Cruise in Rhodes with unlimited drinks & snacks

Kallithea springs is a popular swimming spot. The thermal springs of Kallithea in Rhodes were known from the ancient times for the beneficial properties of...

3 hours • Free Cancellation
4.9 (70)
from
$41
Private Full/Half-Day Boat Trip in Greece with Food and Drinks

Are you looking for a personal experience where you get to steer the boat and trim the sails? Join us and feel the peace of …More

Rhodes, Greece
5.0 (38)

Private Full/Half-Day Boat Trip in Greece with Food and Drinks

Are you looking for a personal experience where you get to steer the boat and trim the sails? Join us and feel the peace of...

5 hours 30 minutes • Free Cancellation
5.0 (38)
from
$614
Rhodes sea cruises (6 hours pleasure cruise with lunch)

''ALKMINI'' boat is a traditional greek wooden motor and sail boat.Its 20 meter long with 3 main engines.Has two decks,one with shadow and the other …More

Rhodes, Greece
4.7 (36)

Rhodes sea cruises (6 hours pleasure cruise with lunch)

''ALKMINI'' boat is a traditional greek wooden motor and sail boat.Its 20 meter long with 3 main engines.Has two decks,one with shadow and the other...

6 hours • Free Cancellation
4.7 (36)
from
$53
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Aboard Sailing Edisa, elegant comfort meets the beauty of Kallithea Springs, where crystal waters invite swimming and …More

Rhodes, Greece
5.0 (18)

Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Aboard Sailing Edisa, elegant comfort meets the beauty of Kallithea Springs, where crystal waters invite swimming and...

4 hours • Free Cancellation
5.0 (18)
from
$1,095

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
An amazing experience
New York City
Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours
catherinecC4601QL, Sep 2026
An amazing experience
We travelled together as a group of 7 including two couples, ages ranged from 26-29. We had a fantastic time onboard, the crew were lovely, helpful and fun. The stops were so beautiful and we had a great time swimming/snorkelling!! The boat has a max of 35 but it didn’t feel full, if you like the sun, there’s room further above the 2nd step up. There’s a lovely cave on the 3rd stop but if you go inside the cave. I HIGHLY recommend swimming shoes as the rocks are rough on your feet or, swim back out instead of climbing over too many rocks to get out on the other side like us🥲. The food was phenomenal, though the white wine is watered down or just tastes more like water, not sure which one. Overall we had a great experience, the music was great, the stops were amazing and the crew were fantastic, thank you so much for a great experience
Read more
Rockin' in Rhodes
New York City
Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours
Dean_C, Sep 2026
Rockin' in Rhodes
Panos was very kind, funny and knowledgeable. Book with full confidence on any cruise! Good food, too!
Read more
Fantastic day out.
New York City
Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim
958iaina, Sep 2026
Fantastic day out.
A fantastic day. We visited 2 small coves and sailed for around 90 minutes each way. Then spent the rest of the time relaxing at anchor. The 2 places we went to were beautifal, blue seas and plenty of fish to snorkel through. The 2 members of staff were brilliant, funny and knowledgeable, both knew a lot and answered questions about thr area and the trip. Lunch was a lovely homemade greek style food, more than enough for us all. There was 13 people on the yacht, varied nationalities and a mix of groups and couples.Would highly recommend, a good day out and would do it again.
Read more
Amazing
New York City
Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks
hollylA237VA, Sep 2026
Amazing
The guide was so lovely and made the trip. She was really engaging and even helped me into the water when I needed the encouragement. Thank you so much!The BBQ was unreal.
Read more
What a trip what a day on the Catamaran
New York City
Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim
Akwright008, Sep 2026
What a trip what a day on the Catamaran
From start to finish the experience was second to none. From inquiring to ultimately returning from the day aboard the boat. Staff I booked through where tentative and made things clear and well put. However the crew on the Catamaran were quite simply second to non. They were a-tentative catered to all our needs in the party of 8. From drinks to food to safety they had it all covered. Yes it’s expensive but worth every penny to be on a private trip even the music on board was a good choice. Highly recommended .
Read more
Enjoy the Bays of Rhodes
New York City
All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea
revhoney, Sep 2026
Enjoy the Bays of Rhodes
11 of us had a great time with Georgios and Monica aboard a sailing yacht. We visited three beautiful bays and enjoyed swimming and a delicious lunch. We highly recommend this tour - we couldn’t have asked for a better time!
Read more
Amazing
New York City
Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks
Barbara_S, Sep 2026
Amazing
This was one of our best days in Greece. The boat ride, the staff, the food and the day on the water was spectacular.When we got off on the island we very much enjoyed it. If I was to make one recommendation is when we got off on the islands if would have a little map to see where we were going that would have been nice. But I would recommend this tour 100% to anyone. We absolutely loved it
Read more
Sailing Edisa
New York City
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne
kaneh713, Sep 2026
Sailing Edisa
Sailing Edisa cannot recommend it enough. Great experience as well as 10/10 hospitality. Food was also amazing and so tasty as the pictures show.We enjoyed it so much we also booked for the following day, however this time we chosen to do the deluxe sunset dinner. This was also fantastic as the views were amazing. We enjoyed so much that we will be visiting again next year for this premium experience!
Read more
A fantastic day onboard GinTonic
New York City
Private Full/Half-Day Boat Trip in Greece with Food and Drinks
F6408KVpaulc, Sep 2026
A fantastic day onboard GinTonic
What a great day we all had, onboard the GinTonic with Georgios. Private sailing for just our family, brilliant swim stops and caves, taking the wheel, absolutely incredible food, the drinks flowed and the weather was perfect.Georgios is a fantastic captain and host, and even let us extend by another hour as we were enjoying ourselves so much and we could easily have stayed longer!Would highly recommend, and we will sail with Georgios on the GinTonic again soon.
Read more
Great day out for sun and swimming.
New York City
Private Full-Day Cruise in Rhodes with Lunch and Drinks
gunnerstar, Sep 2026
Great day out for sun and swimming.
A fabulous day with simi and flori. They were excellent! We were well looked after all day. We would all highly recommend this trip!
Read more
Incredible Sunset
New York City
3-Hours Sunset Catamaran Cruise with Dinner all Inclusive
Yogesh_P, Sep 2026
Incredible Sunset
Incredible views of the sunset, unforgettable memories. Very comfortable seating area and staff were amazing and kind.
Read more
Brilliant boat trip
New York City
All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea
brogang136, Sep 2026
Brilliant boat trip
We went on the Romantika Exclusive Day Cruise. It was brilliant. Not to busy. Fantastic swimming spots. Lovely crew/ staff. Good was delicious. Boat was gorgeous. Great music. Would highly recommend.
Read more
Private luxury boat trip
New York City
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail
G3818QHmeganc, Sep 2026
Private luxury boat trip
Had a private boat trip today with Edward & Isabella, wonderful experience would highly recommend! Beautiful food and amazing time swimming and snorkelling x
Read more
Private luxury sailing boat round rhodes
New York City
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail
nickee2025, Sep 2026
Private luxury sailing boat round rhodes
I booked this fantastic day trip to sea, I checked the reviews to choose and we couldn’t have been any happier. The day was absolutely lovely, we were met by Isabella and captain Edward and taken to the boat, we had a great day just the four of us with Isabella and captain Edward, so a private luxury day relaxing and enjoying the Day. We had a fabulous freshly made cocktail and then followed by a stunning fresh lunch made personally by Isabella. We had local gorgeous Wine , water and then local Greek champagne which was again gorgeous and home grown dragon fruit. We couldn’t have asked for a better day!If you are looking to book a private and luxurious day trip with all the amazing treats and service all included for you and your family or friends as a private day trip we couldn’t recommend Sailing Edisa this day more xxx all enjoy as much as we have xx thank you Isabelle and captain Edward
Read more
Wonderful sail!
New York City
Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim
Bluewater777, Sep 2026
Wonderful sail!
We had a lovely day with Sail Kos - highly recommend if you are looking for a small group sail. Petra was amazing. Informative and helpful. The food was excellent. We went swimming in 2 beautiful coves off of Pserimos. We sailed some on the way there and back. We’re always happy when we get to sail and not motor sail. It was a wonderful day!
Read more
Great private luxery sunset cruise!
New York City
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne
Navigator29611069976, Sep 2026
Great private luxery sunset cruise!
Today, we enjoyed a fantastic private luxury sunset cruise with Sailing Edisa, hosted by Captain Edward and his lovely wife, Isabelle.We received a warm welcome right from the start and were given a fascinating overview of the boat's history. Along the way, we stopped at the Kallithea Springs, where we enjoyed a wonderful swim. Every detail was taken care of—they even provided the necessary swimming gear.After our swim, we were treated to delicious homemade Vietnamese spring rolls, fresh fruit, and a tasty cocktail, all served on a beautifully decorated table. We even got to taste dragon fruit for the first time—a unique fruit grown by Captain Edward himself.Afterwards, we were invited to sit next to the captain and enjoy a glass of champagne as the sun slowly set. It was a truly beautiful moment!And as if that weren't enough, they surprised us with a bottle of delicious wine to celebrate our wedding anniversary. Such a wonderful, thoughtful gesture!Edward and Isabelle make you feel welcome immediately, turning the boat trip into so much more than just an ordinary excursion. Personal service, beautiful moments, great food and drinks, and a stunning sunset.Highly recommended! If you are in Rhodes, you absolutely must experience this cruise.
Read more
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